WO1991017974A1 - Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage - Google Patents

Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage Download PDF

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Publication number
WO1991017974A1
WO1991017974A1 PCT/EP1991/000863 EP9100863W WO9117974A1 WO 1991017974 A1 WO1991017974 A1 WO 1991017974A1 EP 9100863 W EP9100863 W EP 9100863W WO 9117974 A1 WO9117974 A1 WO 9117974A1
Authority
WO
WIPO (PCT)
Prior art keywords
esters
fatty acids
alkanolamines
carbon atoms
quaternized
Prior art date
Application number
PCT/EP1991/000863
Other languages
German (de)
English (en)
Inventor
Günter Uphues
Uwe Ploog
Rainer Jeschke
Peter Waltenberger
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to DE59107391T priority Critical patent/DE59107391D1/de
Priority to US07/949,260 priority patent/US5296622A/en
Priority to EP91909255A priority patent/EP0528899B1/fr
Priority to JP91508466A priority patent/JPH05507073A/ja
Publication of WO1991017974A1 publication Critical patent/WO1991017974A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the invention relates to quaternized esters obtainable by reacting unsaturated fatty acids which have a content of at least 40 ol% trans-configured double bonds, or their esters with alkanolamines and subsequent quaternization of the reaction products with alkylating agents and the use of the products as fabric softening agents .
  • Quaternized esters from saturated fatty acids and alkanolamines are used as softeners in textile finishing [DE-A-1619 058, DE-A-1794068]. Products which are obtainable by reacting 2 moles of saturated fatty acid with 1 mole of triethanola in and subsequent quaternization with dimethyl sulfate or methyl chloride are of particular importance. Textiles that have been treated with quaternized esters of this type have a good soft feel, but they often have an undesirable hydrophobia, which manifests itself in poor wettability or water absorption of the treated fabrics.
  • Quaternized triethanolamine triesters based on saturated or monounsaturated fatty acids with 12 to 22 carbon atoms are known from European patent application EP-A-0239910. Products of this type, which have three long fatty acid residues and a short-chain alkyl group, however, show unsatisfactory conditioning properties.
  • the object of the invention was therefore to develop quaternized esters of fatty acids with alkanolamines which are capable of imparting both good softness to textiles and high hydrophilicity.
  • the invention relates to quaternized esters obtainable from
  • R 1 and R 2 independently of one another represent hydroxyalkyl radicals having 2 to 4 carbon atoms and R- is R ** - or a linear or branched alkyl radical having 1 to 22 carbon atoms and
  • the invention is based on the knowledge that quaternized esters of fatty acids, which are present at least 40 mol% with trans-configured double bonds, impart a surprisingly good soft feel to alkanolamines in the finishing treatment and, moreover, have a less hydrophobic effect.
  • Particularly suitable fatty acids for the production of the quaternized esters according to the invention are elaidic acid and technical fatty acid fractions rich in elaidic acid, some of which Have content of fatty acids with trans-configured double bonds of at least 40 mol%.
  • esters of the abovementioned fatty acids with alcohols having 1 to 4 carbon atoms are also suitable. Typical examples are ethyl, n-propyl, i-propyl, n-butyl or in particular methyl esters.
  • the fatty acids can furthermore be present as full or partial esters of glycerol.
  • the unsaturated fatty acids with a trans-configured double bond content of at least 40 mol% or their esters one can start from linoleic acid or its esters, which selectively select mixtures of monounsaturated fatty acids with high elaidic acid content in the presence of modified nickel catalysts ("trans content") or their esters are hydrogenated.
  • trans content modified nickel catalysts
  • Another possibility is to isomerize cis-octadecenoic acid (oleic acid) or its ester in the presence of selenium or nitric acid to trans-octadecenoic acid (elaidic acid) or its ester.
  • Such methods for the production of elaidic acid and elaidic acid esters have long been known and z. B. in Fette, Seif., Anstrichmitt., 88, 387 (1987) or J.Am.Chem.Soc, 79, 4765 (1967).
  • Quaternized esters with particularly good performance properties are obtained if technical elaidic acid mixtures with a content of at least 40 mol%, preferably at least 50 mol%, in particular more than 60 mol% of elaidic acid, are obtained with alkanolamines of the formula (I) and the reaction products are then quaternized with alkylating agents.
  • Suitable alkanolamines are di- and trialkanolamines and mixtures thereof. Typical examples are methyldiethanola in, ethyldiethanolamine, cocoalkyldiethanola in, methyldiisopropanolamine or triethanolamine.
  • Quaternized esters with particularly good performance properties are obtained if the unsaturated fatty acids are reacted with alkanolamines of the formula (I) in which R * - * , R 2 and R3 represent a hydroxyethyl radical, and the reaction products are then reacted with alkylating agents quaternized.
  • the invention further relates to a process for the preparation of quaternized esters, in which
  • R * and R 2 represent hydroxyalkyl radicals having 2 to 4 carbon atoms and R3 represents Rl or a linear or branched alkyl radical having 1 to 22 carbon atoms, converts and
  • reaction products are then quaternized with alkylating agents.
  • the reactants can be used in a molar ratio of fatty acid to alkanol in from 1.2: 1 to 2.5: 1. Quaternized esters with particularly good performance properties have an average of two ester groups. It is therefore advantageous to carry out the reaction with a molar ratio of 1.5 to 2.5, in particular 1.9 to 2.2.
  • esters of unsaturated fatty acids are used, a transesterification takes place with the alkanolamines.
  • the above-mentioned conditions apply to the amounts of the reactants used.
  • the molar amounts used relate to the molar amount of the fatty acid residues present in the fatty acid glycerol esters.
  • the esterification of the fatty acids with the alkanolamines can be carried out at a temperature of 150 to 220 ° C.
  • An opti a- The reaction rate is achieved when the reaction is carried out in the range from 180 to 200.degree. The reaction is continued until the reaction product has an acid number less than 5.
  • the transesterification of the fatty acid esters with the alkanolamines can be carried out at lower temperatures of 80 to 220, preferably 80 to 150 ° C., in the presence of 0.1 to 0.5% by weight of a basic catalyst, e.g. B. sodium methylate, are carried out. If desired, the alcohol formed in the reaction can be removed by distillation prior to quaternization of the esters.
  • a basic catalyst e.g. B. sodium methylate
  • the crude product is a reaction with alkylating agents, in particular with linear or branched C 3 -C 3 -alkyl or C 1 -C 4 -aryl aralkyl analogs, phosphanes or sulfates such as, for. B. methyl chloride, benzyl chloride, trimethyl phosphate or preferably dimethyl sulfate.
  • alkylating agents in particular with linear or branched C 3 -C 3 -alkyl or C 1 -C 4 -aryl aralkyl analogs, phosphanes or sulfates such as, for. B. methyl chloride, benzyl chloride, trimethyl phosphate or preferably dimethyl sulfate.
  • the quaternization can be carried out in bulk or in solvents, such as. B. water or lower alcohols, at temperatures of 60 to 120, preferably 80 to 100 ° C. To ensure that the quaternization product is free from unreacted alkyl
  • Quater ⁇ nated esters in which the quaternary nitrogen atom has two long-chain and two short-chain substituents for example compounds which by esterification of triethanolamine or methyldiethanolamine with an average of two moles of unsaturated fatty acid and subsequent quaternization with, have particularly good performance properties Dimethyl sulfate can be obtained.
  • the quaternized esters give the fabrics a good soft feel and high hydrophilicity. They are therefore suitable as softening agents for textiles and as fabric softeners and for the production of fabric softeners and laundry detergents.
  • Fatty acid A was produced by selective hydrogenation of technical sunflower fatty acid with a content of 62% by weight linoleic acid in the presence of modified nickel catalysts according to the method described in Fette, Seif., Anstrich ⁇ itt., 88, 387 (1987). Fatty acid A had a trans content of 62% by weight after the selective hydrogenation.
  • reaction product 250 g were transferred to a 500 ml four-necked flask equipped with a stirrer, internal thermometer, dropping funnel and reflux condenser and quaternized with 37.9 g of dimethyl sulfate at 80 to 85 ° C. in the course of 1.5 hours.
  • the reaction mixture was stirred at 85 ° C. for 1 h.
  • 387 g of a semi-solid product were obtained, the degree of quaternization of which, determined by difference formation after two-phase titration in the acidic and alkaline medium, was 84% by weight.
  • 80 g of the quaternized product and 320 g of water were stirred at 80 ° C. for 30 minutes to form a finely divided dispersion and then cooled to 20 ° C. (product A *).
  • Example 1 was repeated using technical fatty acid with high (fatty acids B and C, examples 2 and 3) or low trans content (fatty acids D and E, comparative examples 1 and 2). The products B * to E * were obtained. III. Application examples
  • Cotton terry toweling fabric was finished under the same conditions. The evaluation of the soft grip showed comparable results to the molton fabric.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Par la réaction d'acides gras monoéthènoïdes présentant une teneur d'au moins 40 % molaires en liaisons doubles transconfigurées, ou de leurs esters avec des alkamines et quaternation subséquente des produits réactionnels avec des agents d'alkylation, on obtient des esters quaternés possédant des propriétés adoucissant le textile et hydrophilisantes.
PCT/EP1991/000863 1990-05-17 1991-05-08 Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage WO1991017974A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE59107391T DE59107391D1 (de) 1990-05-17 1991-05-08 Quaternierte ester von alkanolaminen mit fettsäuren und verwendung als avivagemittel
US07/949,260 US5296622A (en) 1990-05-17 1991-05-08 Quaternized esters
EP91909255A EP0528899B1 (fr) 1990-05-17 1991-05-08 Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage
JP91508466A JPH05507073A (ja) 1990-05-17 1991-05-08 アルカノールアミンと脂肪酸から得られる四級化エステルおよび回復剤としてのその使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4015849A DE4015849A1 (de) 1990-05-17 1990-05-17 Quaternierte ester
DEP4015849.7 1990-05-17

Publications (1)

Publication Number Publication Date
WO1991017974A1 true WO1991017974A1 (fr) 1991-11-28

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PCT/EP1991/000863 WO1991017974A1 (fr) 1990-05-17 1991-05-08 Esters quaternes obtenus a partir d'alkamines et d'acides gras, et utilisation de ces esters comme agent d'avivage

Country Status (11)

Country Link
US (1) US5296622A (fr)
EP (1) EP0528899B1 (fr)
JP (1) JPH05507073A (fr)
AT (1) ATE133937T1 (fr)
AU (1) AU7851591A (fr)
CA (1) CA2083180A1 (fr)
DE (2) DE4015849A1 (fr)
DK (1) DK0528899T3 (fr)
ES (1) ES2083574T3 (fr)
TR (1) TR24940A (fr)
WO (1) WO1991017974A1 (fr)

Cited By (14)

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Publication number Priority date Publication date Assignee Title
FR2685649A1 (fr) * 1991-12-31 1993-07-02 Stepan Europe Tensioactifs a base de composes d'ammonium quaternaire, procede de preparation, bases et compositions assouplissantes derivees.
EP0550361A1 (fr) * 1991-12-31 1993-07-07 Stepan Europe Tensioactifs à base de composés d'ammonium quaternaire, procédés de préparation, bases et compositions assouplissantes dérivées
FR2688419A1 (fr) * 1992-03-12 1993-09-17 Stepan Europe Base tensioactive comprenant un compose cationique d'ammonium quaternaire et un compose a titre de solvant et composition assouplissante comprenant une telle base.
WO1993021291A1 (fr) * 1992-04-10 1993-10-28 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement aqueux a faible viscosite, pour textiles
FR2693665A1 (fr) * 1992-07-17 1994-01-21 Stepan Europe Compositions tensioactives cationiques, à base de mono ou polyalkyl ester et/ou amido ammonium, et leurs procédés de préparation.
EP0604726A1 (fr) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Procédé de quaternisation d'esters triéthanolaminiques d'acides gras et d'imidazolinamides avec des graisses et huiles alcoxylées comme milieu réactionnel et l'utilisation des melanges réactionnels comme composants d'un agent adoucissant
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EP0644179A1 (fr) * 1993-09-17 1995-03-22 Stepan Europe Base tensioactive comprenant un composé cationique d'ammonium quaternaire et un composé à titre de solvant et composition assouplissante comprenant une telle base
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
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EP0550361A1 (fr) * 1991-12-31 1993-07-07 Stepan Europe Tensioactifs à base de composés d'ammonium quaternaire, procédés de préparation, bases et compositions assouplissantes dérivées
FR2685649A1 (fr) * 1991-12-31 1993-07-02 Stepan Europe Tensioactifs a base de composes d'ammonium quaternaire, procede de preparation, bases et compositions assouplissantes derivees.
FR2688419A1 (fr) * 1992-03-12 1993-09-17 Stepan Europe Base tensioactive comprenant un compose cationique d'ammonium quaternaire et un compose a titre de solvant et composition assouplissante comprenant une telle base.
WO1993021291A1 (fr) * 1992-04-10 1993-10-28 Henkel Kommanditgesellschaft Auf Aktien Agents de traitement aqueux a faible viscosite, pour textiles
FR2693665A1 (fr) * 1992-07-17 1994-01-21 Stepan Europe Compositions tensioactives cationiques, à base de mono ou polyalkyl ester et/ou amido ammonium, et leurs procédés de préparation.
EP0580527A1 (fr) * 1992-07-17 1994-01-26 Stepan Europe Compositions tensioactives cationiques, à base de mono ou polyakyl ester et/ou amido ammonium, et leurs procédés de préparation
EP0604726A1 (fr) * 1992-12-23 1994-07-06 Hüls Aktiengesellschaft Procédé de quaternisation d'esters triéthanolaminiques d'acides gras et d'imidazolinamides avec des graisses et huiles alcoxylées comme milieu réactionnel et l'utilisation des melanges réactionnels comme composants d'un agent adoucissant
US5443631A (en) * 1992-12-23 1995-08-22 Huels Aktiengesellschaft Process for the quaternization of triethanolamine fatty acid esters and imidazolinamides and the use of the reaction mixtures in laundry softener compositions
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
WO1994020597A1 (fr) * 1993-03-01 1994-09-15 The Procter & Gamble Company Compositions adoucissantes pour tissus concentrees et biodegradables a base d'ammonium quaternaire et composes contenant des chaines d'acide gras insature a indice d'iode intermediaire
US5574179A (en) * 1993-03-01 1996-11-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains
US5562849A (en) * 1993-03-01 1996-10-08 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
EP0644179A1 (fr) * 1993-09-17 1995-03-22 Stepan Europe Base tensioactive comprenant un composé cationique d'ammonium quaternaire et un composé à titre de solvant et composition assouplissante comprenant une telle base
US5463094A (en) * 1994-05-23 1995-10-31 Hoechst Celanese Corporation Solvent free quaternization of tertiary amines with dimethylsulfate
WO1995034620A1 (fr) * 1994-06-13 1995-12-21 Henkel Kommanditgesellschaft Auf Aktien Dispersions aqueuses de tensioactifs anioniques et cationiques
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
WO1998047991A1 (fr) * 1997-05-19 1998-10-29 The Procter & Gamble Company Agent adoucissant derive de triethanolamine acyle
US6486121B2 (en) 1998-04-15 2002-11-26 The Procter & Gamble Company Softener active derived from acylated triethanolamine
DE10351111A1 (de) * 2003-11-03 2005-06-16 Langlotz, Rainer Arzneimittel und Verfahren zu ihrer Herstellung

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CA2083180A1 (fr) 1991-11-18
US5296622A (en) 1994-03-22
ES2083574T3 (es) 1996-04-16
DE59107391D1 (de) 1996-03-21
AU7851591A (en) 1991-12-10
TR24940A (tr) 1992-07-01
JPH05507073A (ja) 1993-10-14
EP0528899B1 (fr) 1996-02-07
DE4015849A1 (de) 1991-11-21
DK0528899T3 (da) 1996-06-10
EP0528899A1 (fr) 1993-03-03
ATE133937T1 (de) 1996-02-15

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